Acetonitrile → HCID 21252806, compound

HRID 848974Notes

Reaction equation

HRID 848974 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([C:16]([O-:18])=[O:17])=[CH:13][NH:14][N:15]=2)=[CH:6][CH:5]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1.[C:34](#N)[CH3:35]>>[F:20][C:2]([F:1])([F:19])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[N:15]([C:30]([NH:29][C:26]3[CH:25]=[CH:24][C:23]([C:22]([F:32])([F:33])[F:21])=[CH:28][CH:27]=3)=[O:31])[NH:14][CH2:13][CH:12]([C:16]([O:18][CH2:34][CH3:35])=[O:17])[O:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 86755016HCID 86755016, compound

Product 1

HCID 21252806HCID 21252806, compound

Procedure

1 g of the ethyl 5,6-dihydro-2-(4-trifluoromethoxy-phenyl-4H-1,3,4-oxadiazine-6-carboxylate prepared above in A was dissolved in 15 ml of acetonitrile. 1 g of 4-(trifluoromethyl)phenyl isocyanate was added dropwise. The resulting reaction mixture was refluxed for two hours and then the solvent was evaporated under reduced pressure to produce a solid. The solid was washed with a few milliliters of acetonitrile to produce 1.2 g of ethyl 5,6-dihydro-2-(4-trifluoromethoxyphenyl)-N-(((4-trifluoromethylphenyl)amino)carbonyl)-4H-1,3,4-oxadiazine-6-carboxylate as a white solid. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for two hours
  3. customthe solvent was evaporated under reduced pressure
  4. customto produce a solid
  5. washThe solid was washed with a few milliliters of acetonitrile

Sources & evidence

ORD record
ord-f80c1f7ba8e2452ea3f031bc023cf8fa
Source dataset
uspto-grants-2000_01
Patent number
US06011034

Reaction notes

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